In Fincastle, there’s now a big hole in downtown where the courthouse used to stand.
Behind that is another hole, although it’s harder to see. It’s a hole in the heart of those who care about history.
The courthouse, which looked historic but was not (it dated to the early 1970s), will be replaced.
The smaller brick building behind it, which was historic, will be replaced, too — by a replica.

That building was the law office of James Breckinridge, one of those figures in history who had connections to some of the giants in our history — he studied law under George Wythe, he was involved with his friend Thomas Jefferson in founding the University of Virginia — but today is barely known.
Well, barely known outside Botetourt County, where the demolition of his old law office was for a time this summer a minor controversy. In the end, uncomfortable facts won out over sentiment: The building was in the way of building a new courthouse. There had been talk about moving the structure but then the building was deemed in such poor condition that if anyone tried to move it, the whole thing would collapse into dust. The solution, which seemed to appease even those in what some local wags call “hysterical Fincastle” rather than “historical Fincastle,” was to take the building down and then build a replica. (Disclosure: I live outside Fincastle, although, in the context of Botetourt County, there’s a big difference between living “near Fincastle” and living “in Fincastle.”)
Now that the dust has settled — and in this case, actual dust, which had to be watered down to keep it from blowing over the town — it seems appropriate to dig deeper into this 18th- and 19th-century figure whose name still adorns an elementary school in Fincastle and whose law office was deemed worthy of saving, even in replica form.
His resume checks off almost every important box of his era: He was the son of an immigrant from Ireland, as many in “the Great Valley” were. As a late teenager, he enlisted in the Continental Army and served under Gen. Nathanael Greene in his North Carolina campaigns against Lord Cornwallis. After the war, he attended Liberty Hall Academy in Lexington (what today we know as Washington & Lee University) and later went off to Williamsburg to study law. He came back to Fincastle in 1789 and did all the usual things a rising young man with political connections and ambitions might do: He was named a captain in the county militia, won election to the House of Delegates, got married and built a grand estate just outside town. He’s said to have entertained the explorers Meriwether Lewis and William Clark when they passed through Fincastle.
All that’s well and good, the dry recitation of historical markers (which Breckinridge strangely lacks). Now, here’s the drama: For most of his political career, Breckinridge was in the political minority in Virginia, which makes his career all the more remarkable.
Breckinridge was a devoted Federalist in a state that was decidedly anti-Federalist. Eventually those anti-Federalists coalesced into what was called then the Democratic-Republican Party (but which has nothing to do with either Democrats or Republicans today). Federalists nominated Breckinridge as their candidate for the U.S. Senate in 1796; he lost (this was at a time when state legislatures still picked senators). He was the Federalist candidate for governor in 1799; he lost that, too (this was at a time when the legislature picked governors, too).

Whether you identify with Republicans today (in the minority in the General Assembly) or Democrats (in the minority in Congress), Breckinridge was your guy — the leader of the opposition. They say history is written by the winners (with the obvious exception of the Southern version of the Civil War) and the winners in those days were people with last names like Jefferson, Madison, Monroe. No wonder Breckinridge doesn’t get his due in history. In 1800, Breckinridge was a Federalist candidate for one of Virginia’s electors, which meant that he was supporting President John Adams over native son Thomas Jefferson.
For those who think elections should take place on a single day with none of this early voting business, just remember that wasn’t the tradition then. The election of 1800 in Virginia lasted more than a month, from Oct. 31 to Dec. 3, because there was no set date statewide. Every county had its own Election Day. Jefferson carried Virginia in a landslide, with 77% of the vote to just under 23% for Adams. The few places where Adams won were mostly in modern-day West Virginia. Jefferson even won handily in Botetourt County; that’s how out-of-step Breckinridge was with his fellow Virginians. They still loved him in Botetourt, though, because voters there again sent him back to the House of Delegates, where Democratic-Republicans remained in control.

Then Breckinridge set his sights higher. He ran for Congress — although there’s some dispute as to when. Encyclopedia Virginia says he ran a “poorly organized campaign” and lost in 1806; Early American Elections doesn’t list him as a candidate but doesn’t list anyone who received less than 5% of the vote, so maybe Breckinrige’s bid really was that bad. If he did run in 1806, he was definitely running in a bad year for Federalists.
Today congressional midterms typically work against the president’s party. That was not the case then. President Thomas Jefferson was in his second term. His Democratic-Republicans had a supermajority in the House; the 1806 elections saw Jefferson’s party gain seats. Democratic-Republicans that year won 22 ofVirginia’s 23 seats in the U.S. House of Representatives (ah, those were the days), with Federalists holding on only to the seat that represented what today we call Northern Virginia.
Don’t try to translate the parties then into the parties now because they won’t line up. The Federalists wanted a strong central government (which would seem to make them akin to today’s Democrats) but they were also ardent protectionists (which would put them in alignment with Donald Trump today). Federalists tended to be the party of cities and manufacturers, Democratic-Republicans the party of rural areas and farmers, but those lines weren’t clear-cut because Fincastle wouldn’t be mistaken for a city even today. On the great foreign policy questions of the day, Federalists identified more with Great Britain while Democratic-Republicans tended to be more sympathetic towards France.

Regardless of what may or may not have happened in 1806, Breckinridge ran for Congress in 1808. That year was a presidential year, and James Madison, a Democratic-Republican, won easily over Federalist Charles Pinckney. Democratic-Republicans retained Congress, but saw their majorities in the U.S. House reduced. In Virginia, Federalists flipped four seats. Breckinridge was one of those flippers, ousting Alexander Wilson of Lexington with 56.7% of the vote.
Numerically, Breckinridge was the congressman from the 5th District, which technically makes him the forerunner of John McGuire today, although he lived in Botetourt County, the same as Ben Cline of today’s 6th District does. The 5th District then was an L-shaped mess that started in Rockbridge, went south into Botetourt (which then included what today is Roanoke, Roanoke County, Salem and parts of Alleghany and Craig counties) and then struck out through modern-day West Virginia all the way to the Ohio River.
In 1810, Breckinridge was reelected with 58.4% of the vote, then won uncontested races in 1812 and 1814. Breckinridge was in the minority throughout his four terms in Congress and, while it wasn’t immediately clear at the time, the Federalists were a dying party. Sometimes the key elections were between different factions of Democratic-Republicans. In Congress, Encyclopedia Virginia says, Breckinridge “seldom spoke in Congress but kept his constituents informed of his Federalist foreign policy views, including fear of Napoleon’s expansionistic schemes.”
Breckinridge’s tenure coincided with growing tensions with Great Britain, which challenged the Federalists’ worldview. He voted against declaring what we remember today as the War of 1812 (and still misnamed because it lasted for more than one year). When the British burned Washington, the Botetourt County militia was called into service — and so Rep. Breckinridge temporarily became Gen. Breckinridge. “His regiment crossed the Potomac River into Maryland and encamped until the danger of further damage from the British fleet was over and his troops were sent home that December,” Encyclopedia Virginia says.
With the war over, and the Federalists in disarray, Breckinridge may have lost his interest in national politics — but not state ones. He presided over a meeting in Staunton where Virginia’s western counties tried to figure out how to wrest power away from eastern ones (they failed and nearly a half-century later the result would be West Virginia). Breckinridge didn’t seek reelection in 1816 but ultimately returned to the House of Delegates in 1819.
The curious thing is that this Federalist became friends with the premier anti-Federalist, Jefferson. By then, Jefferson was long out of office — and keen to start a university. Between leaving the U.S. House and returning to the Virginia House, Breckinridge was named one of the commissioners to help pick a site for Jefferson’s proposed university. Jefferson sent Breckinridge plans for a new courthouse in Fincastle (that courthouse is long gone, but subsequent courthouses were designed to look like it, so Botetourt still claims it has a courthouse designed by Jefferson). In one letter in 1818, Jefferson lamented that he and Breckinridge met so late in life. “I only lament that the knowledge of your worth and goodness comes to me when so little of life remains to cultivate and to merit its cordial reciprocation,” Jefferson wrote. The former president was recovering from an illness at the time but promised that if he recovered, he would make one of his “annual rambles to the Natural Bridge” and then “extend them to Fincastle, towards which the pleasure of visiting you would be the chief inducement.” (The visit doesn’t appear to have ever happened.)
In 1819, Gov. James Patton Preston — a Democratic-Republican — appointed Breckinridge to the board of visitors of the university, a position he held until his death in 1833. (These days a legislator couldn’t serve on a university board. It would also be highly unusual for a governor of one party to appoint someone of another to such a prestigious position. There are also term limits on board service. So, yeah, lots of things have changed.) Back in the legislature, Del. Breckinridge “used his influence to push through the assembly a loan bill for the university, thus enabling the construction of buildings to proceed,” Encyclopedia Virginia says.

Long after the Federalists were gone as a party, Breckinridge held onto some Federalist ideals, such as government support for “internal improvements,” what today we’d call infrastructure spending. Today that might mean roads; then it meant roads and canals, especially the James River and Kanawha Canal, which eventually got as far as Buchanan in Botetourt County before the rise of railroads made canals obsolete. Think of canals as the interstate highways of their day.
What should we make of Breckinridge today? It’s always dangerous to read too much of today’s politics into historical figures, but I’m taken by his latter-day friendship with Jefferson, which crossed party lines. I’d like to think we could all learn something from that.
And now, back to today’s politics

We publish a weekly political newsletter, West of the Capital, that goes out on Fridy afternoons. This week we’ll have:
- Medical group in Augusta County closes three offices, cites One Big Beautiful Bill
- Winsome Earle-Sears and Jason Miyares campaign in the western part of Virginia
- A new poll and two new political forecasts
- Lots of photos from Labor Day politicking
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